Holling Hoodhood, a seventh grader at Long Island's Camillo Junior High, is convinced that his teacher, Mrs. Baker, hates him. All of Holling's classmates are members either of St. Adelbert's Catholic Church or Temple Beth-El; Holling alone is Presbyterian. This in itself would not be a problem, except on Wednesdays, when, during the final period of the day, half of the students are excused to attend Hebrew School, while the other half go to Catechism. This leaves only Holling in class with Mrs. Baker, and Holling is certain his teacher is not happy about the situation.
Holling lives in what he calls "the Perfect House," located "right smack in the middle of town." This pristine but uninviting dwelling represents the values of his father, an architect at Hoodhood and Associates. After his first day of school, Holling goes home looking for an ally in what he perceives will be an upcoming, year-long "war" with Mrs. Baker. Sadly, his mother, a secret smoker, shrugs off his concerns with platitudes, while his father makes it clear that Holling had better not do anything to antagonize Mrs. Baker because he is trying to win a lucrative contract with her family's business. Holling's older sister, locked inside her room listening to the Monkees, is no help either, dismissing him cynically with a cutting jibe.
At school the next day, Holling is certain that Mrs. Baker is plotting to have "something awful" happen to him when he is coerced by the older boys into playing soccer, and is assigned to guard Doug Swieteck's hulking brother. With the behemoth barreling towards him, Holling, his own survival foremost in his mind, runs to the goal, waits, and sidesteps at the last second, inadvertently tripping his opponent and causing him to hit his head with "an iron thunk" against the goal post. Holling's friend Danny Hupfer, and Doug Swieteck himself, are in awe that Holling was able to "take out" Doug's brother, but Meryl Lee Kowalski, whom Holling believes has been in love with him since the third grade, berates him for his behavior. After it is announced on the public address system that Doug Swieteck's brother is fine and "would be back in school after ten days of observation," Mrs. Baker looks at Holling, who is sure she hates his guts.
Holling's paranoia is intensified when he is called to the office to see Mr. Guareschi, the principal. Mrs. Baker has suggested that Holling sit in on a sixth grade mathematics class on Wednesdays, since he had gotten by last year with "a decidedly below-average grade." As Holling had technically passed, however, Mr. Guareschi decides that he is ineligible to take the course again. Mrs. Baker responds to this news impassively, and later that afternoon, Mr. Guareschi announces that "Lieutenant Tybalt Baker would soon be deployed to Vietnam...and (the school community) should wish him, together with Mrs. Baker, well."
During Wednesday afternoons in September, Holling is assigned to do odd jobs by Mrs. Baker, which frequently includes pounding chalkboard erasers. Because of his father, Holling is careful not to complain, and by the first week in October, Mrs. Baker's family business, Baker Sporting Emporium, has narrowed its architect choices to two: Hoodhood and Associates, and Kowalski and Associates. At recess one Wednesday, Mrs. Baker asks Holling to bring up trays of cream puffs that Mrs. Bigio, the campus cook, has made for a gathering of Wives of Vietnam Soldiers. Dutifully, Holling makes twelve trips to the first floor kitchen, carrying the trays one at a time and placing them by the open windows of the third floor seventh grade classroom. When the students leave for their religious education classes,...
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Mrs. Baker gives Holling a big box of erasers to pound. Holling watches the clouds of chalkdust rise in the breeze, and is horrified when he realizes that they are wafting into the open classroom windows and settling gently on the trays of cream puffs. Mrs. Baker gives Holling a cream puff when he has finished, but he surreptitiously disposes of it. It is later rumored that "every single one of the Wives of Vietnam Soldiers had nearly choked to death while eating cream puffs," and while Mrs. Baker clearly suspects Holling knows something about the matter, she does not press the issue. Danny, Meryl Lee, and the others, however, discover that Mrs. Baker has given Holling a cream puff, and threaten him with death if he does not bring one for everyone in the class.
At supper later that week, Holling's sister comes to the table with a yellow flower painted on her cheek. She declares that she is a flower child who believes "in peace...understanding...and helping each other," and asserts that the flower children, who marched that day on the Pentagon to protest the war, are "going to change the world." Holling's father reacts by saying that flower children are nothing more than hippies "in dirty jeans." Mr. Hoodhood tells his daughter that she is hurting his chances of winning the Chamber of Commerce Businessman of 1967 award, and orders her to remove the flower painted on her face. Holling's sister, defeated, reluctantly complies. Later that night, she chides Holling for not sticking up for her. She tells him that "something big is happening" in the country right now, and that he should think about growing up and "becoming who (he is) supposed to be." Holling's sister says that when she looks at him, she sees only the "Son Who Is Going to Inherit Hoodhood and Associates," and wonders why he does not stand up to their father.
At school, Mrs. Baker tells Holling that henceforth, on Wednesday afternoons, she will be teaching him Shakespeare, an announcement which makes Holling envision being "bored to death for eight months." Before they begin, however, Mrs. Baker has one last chore for him; Holling is to clean out the cage of her two large rats, Sycorax and Caliban. Predictably, the rats escape, climbing the radiator into the walls, where they are impossible to apprehend. On the bright side, Holling discovers that Shakespeare is not so bad after all. The first play Mrs. Baker assigns is The Merchant of Venice; Holling is intrigued by the character of Shylock, whom he recognizes as not a villain but a tragic individual who is denied the chance to "become who he's supposed to be" because of the expectations of others.
Wednesday Wars is narrated by the protagonist, Holling Hoodhood. By using this first person device, the author gives the reader an in-depth view of what is going on in Holling's mind. In the opening section, which covers the first two months—September and October—of seventh grade, Holling reveals himself to be a likable, intelligent, but completely self-absorbed young teen. Holling is convinced that, because of a scheduling quirk which requires him to be the only student still in class on Wednesday afternoons, his teacher hates his guts. From his limited perspective, and with a sense of paranoia which is comical in its single-minded intensity, Holling imagines that Mrs. Baker is actively plotting his demise; to him, her every look is meaningful and menacing. Even when the principal announces that Mrs. Baker's husband is about to be deployed to Vietnam, Holling shows his complete inability to see things from other viewpoints when he interprets her impassive reaction not as a mask against grief, but as proof that she is an evil, conniving person out to get him.
It is evident that the setting will play a significant role in the development of the narrative. It is 1967, and the Vietnam War permeates the lives of everyone in the nation. The faculty at Camillo Junior High is intimately affected, as at least two of the staff, Mrs. Baker and Mrs. Bigio, have spouses who are involved in the conflict, and both women are active with the organization "Wives of Vietnam Soldiers." One of Holling's classmates, Mai Thi Huong, is a Vietnamese refugee, and Holling's parents watch Walter Cronkite's news report on the situation in the war zone on CBS nightly. Holling's sister, who is in high school, is drawn to the element of young people actively opposing the war, and her efforts to declare her loyalties leads to confrontations with her father, whose only concerns are his business and his reputation.
The most important scene in these first two chapters is arguably the one that begins at the Hoodhood dinner table and concludes in Holling's room immediately thereafter. Holling's sister joins the family with a bright yellow flower painted on her cheek, and her father's belittling and authoritative response, coupled with his interrogation of Holling about his relationship with Mrs. Baker, establishes definitively his crass and superficial value system. Holling's mother is a nonentity in the proceedings, illustrating her insignificance in the face of her husband's dominance, and Holling himself focuses all his energies on just staying out of trouble. It is Holling's sister who verbalizes what will be the central conflict in the novel, the difficulty of discovering one's own identity and entering into maturity. After supper, Holling's sister tells Holling that she wants his support "for believing in something bigger than just (herself)," and warns him that he, too, should start thinking about growing up, and "becoming who (he is) supposed to be."
A final thread that is introduced is one that concerns the great literary master, Shakespeare. It is no accident that Mrs. Baker's husband is named Tybalt, and her two rats are Caliban and Sycorax, all characters in Shakespeare's plays. Recognizing that Holling is an exceptionally bright and well-read student, Mrs. Baker decides to expose him to Shakespeare, and it is clear from his immediate ability to discern the real tragedy of the character of Shylock from The Merchant of Venice, that Shakespeare's writings will have a major influence on Holling as he faces the challenges of growing up.